Sodium borohydride → HCID 70434749, compound

HRID 1380329Notes

Reaction equation

HRID 1380329 reaction equation
O.[Cl:2][C:3]1[CH:8]=[C:7]([OH:9])[C:6]([Cl:10])=[CH:5][C:4]=1[C:11]([CH:13]=O)=[O:12].[NH2:15][C:16]([CH3:29])([CH3:28])[CH2:17][CH2:18][N:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[N:21]=[CH:20]1.[BH4-].[Na+]>CO>[ClH:2].[ClH:2].[Cl:2][C:3]1[CH:8]=[C:7]([OH:9])[C:6]([Cl:10])=[CH:5][C:4]=1[CH:11]([OH:12])[CH2:13][NH:15][C:16]([CH3:29])([CH2:17][CH2:18][N:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[N:21]=[CH:20]1)[CH3:28]

Participants

5

Reactant 3

HCID 4311764Sodium borohydride2×HCID 20214926HCID 20214926, compoundHCID 20214946HCID 20214946, compound

Product 1

HCID 70434749HCID 70434749, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 9.3 gm of 2,5-dichloro-4-hydroxyphenyl-glyoxal hydrate, 7.25 gm of 1-(3-amino-3-methylbutyl)-benzimidazole and 100 ml of alcohol was stirred for 3 hours at 40°-45° C. The resulting solution was subsequently cooled, admixed in portions with 8 gm of sodium borohydride, and the mixture was stirred for 3 hours at room temperature. After the addition of 100 ml of methanol for decomposition of the sodium borohydride, the mixture was allowed to stand for 10 hours, the solvent was distilled off under reduced pressure, the residue was dissolved in 200 ml of water, and the solution was acidified with concentrated hydrochloric acid. 9.5 gm of 1-(2,5-dichloro-4-hydroxyphenyl)-2-[4-(1-benzimidazolyl)-2-methyl-2-butylamino]-ethanol dihydrochloride×1H2O, m.p. 180°-183° C., of the formula ##STR29## were obtained. The yield was 50.4% of theory.

Workup

  1. temperatureThe resulting solution was subsequently cooled
  2. stirringthe mixture was stirred for 3 hours at room temperature
  3. waitto stand for 10 hours
  4. distillationthe solvent was distilled off under reduced pressure
  5. dissolutionthe residue was dissolved in 200 ml of water
  6. customwere obtained

Sources & evidence

ORD record
ord-e6b474f54bb04834a8bd2b8216c7938e
Source dataset
uspto-grants-1986_04
Patent number
US04581367

Reaction notes

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